Sir Anthony Sherley

Anthony Sherley was a roguein the strictest sense of the word. He was born into a wealthy but was forcedto find his own way after his families property went into bankruptcy. He had anOxford education, but had to take to soldiering, forgoing his education.
In 1591 he went to Normandyas one of the Earl of Essex's soldiers. While there he was knighted by theFrench. In 1593 he was imprisoned until he renounced his foreign title.Striving to rise in stature, he married a cousin of the earl, but soon foundhis wife intolerable. Seeing nothing for him to gain by staying in England, heleft to seek his fortune elsewhere. Sherley used his relation to the earl toaquire funds for an expedition to capture Sβo Thomι, a Portuguese island off the coast of Africa.
In May 1596 Sherleyassembled eight ships carrying about 400 soldiers. The expedition was struck bydisease early in the voyage. Sherley was forced to change his course to thenorth. Sherley took Santiago in the Cape Verde Islands but the booty was verysparse. His force much depleted, Sherley then attacked and took Santa Marta,Colombia. In early 1597, they sacked the poor Jamaican settlement of Santiagode la Vega. Their main purpose in the attack was to replenish supplies. So farthe sum total of booty for his raids was pretty sparse.
While in Jamaica, Sherleymet Captains William Parker and Michael Geare. The two joined with Sherley in an attack uponTrujillo (Honduras), but were unsuccessful. Next they tried their luck inattacking Puerto Caballos, and after taking it, found it to be destitute. Geareleft to seek his fortune. Sherley and Parker, decided to try to march acrossthe Guatemala mountains to the Pacific. Once again they were daunted by theseverity of the trip and chose to take their remaining men through the Straitof Magellan. By this time Sherley's men have lost faith in their captain anddeserted him. With his remaining ship, Sherley went back to England and also totremendous debts.
Toward the end of 1597,Sherley was sent to Ferrara, Italy in the company of English troops. By thetime they arrived the differences between Italy and England were settled andSherley was faced with unemployment. Sherley, once again using his relationshipwith the Earl of Essex, managed to raise enough money to sail to Persia. Heplanned to establish diplomatic relations (without the consent of the crown)with the new shah. The shah made Sherley his ambassador and enlisted him to gainallies against the Ottoman Empire. When Sherley returned to England his planwas condemned and he was forbade to return to Persia. Sherley then made hisrounds from royal court to court and conned nobles out of funds.
In 1607, Sherley managed tobecome an agent of the Spanish. During this time he wrote to Simon Simonson and John Ward trying to sway them to make attacks upon theOttoman Empire. Two years later, in 1609, the Spanish had Sherley assembleships in Sicily to attack the Barbary corsairs. It was planned that Sherleywould join in a Spanish attack on Tunis, but instead Sherley attacked Europeanmerchantmen and looted the Greek Islands. After Sherley's failure to supportSpain's attack on Tunis, he lost all influence in the Spanish courts but stayedin Spain constantly trying to gain political stature. He died destitutein Spain circa 1637.